CN101657413B - 4-dodecene derivatives as perfuming ingredients - Google Patents
4-dodecene derivatives as perfuming ingredients Download PDFInfo
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- CN101657413B CN101657413B CN200880012003XA CN200880012003A CN101657413B CN 101657413 B CN101657413 B CN 101657413B CN 200880012003X A CN200880012003X A CN 200880012003XA CN 200880012003 A CN200880012003 A CN 200880012003A CN 101657413 B CN101657413 B CN 101657413B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/40—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/06—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and unsaturated carbon skeleton
- C07C255/07—Mononitriles
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- Chemical & Material Sciences (AREA)
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- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
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Abstract
The present invention relates to the field of perfumery. More particularly, it concerns specific oxime or nitrile derivatives of 4-dodecene, which are useful perfuming ingredients in particular to impart natural mandarin notes.
Description
Technical field
The present invention relates to field of perfumery.More specifically, relate to specific nitrogenous 4-laurylene derivative as useful perfuming ingredients.The invention still further relates to described compound in perfume industry purposes and contain described compound compositions or goods.
Background technology
As far as our knowledge goes, any compound of the present invention all is unknown.
Known in perfumery corresponding saturated nitriles be that the dodecyl nitrile is used as useful component (referring to S.Arctander, Perfume and Flavor Chemicals, 1969, Montclair, NewJersey, USA, compound N ° 1121).Yet the organoleptics property that described analog has is different from the organoleptics property of nitrile of the present invention fully.And, enumerated in the prior art of this analog and shown not or indicated that this compound can be used as perfuming component, their special fragrance is not discussed especially yet.
Summary of the invention
We now have been surprisingly found out that and the compound of general formula (I) can be used as perfuming component, for example give the smell aromatic of orange,
Wherein X represents CN or HN=OH group, carbon-carbon double bond be configured as E or Z or their mixed form.
As mentioned above, compound (I) can be the form of its E isomer or Z isomer, or or even their mixed form.Specific embodiments according to the present invention, the compound of the general formula of valuing especially (I) are those isomer (4Z) and (4E) mixed form of ratio in 80/20～99.5/0.5 scope.According to another embodiment of compound (I), carbon-carbon double bond be configured as Z.
As the specific examples of The compounds of this invention, specifiable is (4Z)-4-laurylene nitrile, and it has strong, special natural orange smell, and this smell is generally ripe orange and fruit juice thereof to be owned.
The spices dealer has the interest of being very glad for the smell of described nitrile, because known considerably less compound has the orange smell, i.e. and (4Z)-4-dodecylene aldehyde and sinensal (Sinensal, namely 2,6,10-trimethylammonium-2 (E), 6 (E), 9 (E), 11-12 carbon tetraene-1-aldehyde).
(4Z)-smell of 4-laurylene nitrile allows the people remember the sinensal smell of (it has very different chemical structures and is very difficult to preparation).
But, when with the smell of The compounds of this invention with (4Z)-during the contrast of the smell of 4-dodecylene aldehyde, great sense of smell difference has unexpectedly appearred.For example (4Z)-4-laurylene nitrile has the natural, gentle of how typical mature fruit and stable smell, and (4Z)-4-dodecylene aldehyde has acid, the feature of dashing of typical not mature fruit, and wherein typical " dog is disturbed flavor " (wet dog) aspect of mature fruit compares more not obvious in the smell of this nitrile.In other words, the allotment ability of spices dealer to the orange aromatic that the smell that has of nitrile of the present invention is perfect.
When the smell of (4Z)-4-laurylene nitrile and the contrast of its saturated nitriles analogue dodecyl nitrile, difference is more surprising.In fact, (4Z)-4-laurylene nitrile do not have the very typical herbal medicine of dodecyl nitrile, fat or wooden aromatic.In addition, the dodecyl nitrile compound only makes us remembering orange peel faintly, but not as orange.
As another specific examples of The compounds of this invention, can enumerate (4Z)-4-laurylene aldoxime, it has given the orange that has not mature slightly feature aromatic.The smell of this class oxime is compared not obvious with the smell of nitrile above-mentioned.
As mentioned above, the present invention relates to general formula (I) compound as the purposes of perfuming component.In other words, the present invention relates to give, strengthen, improve or change perfume composition or the adour properties of perfumed article, this method comprises to described composition or goods adds at least a general formula (I) compound of significant quantity.According to specific embodiments of the present invention, described method or purposes are valued especially because giving orange odor type smell aromatic.
Here, " purposes of general formula (I) compound " also must be understood that arbitrary purposes that contains the composition of compound (I), and it can be advantageously used in the perfume industry as activeconstituents.
In fact, the described composition that can be advantageously used for perfuming component also is one object of the present invention.
Therefore, another object of the present invention is a kind of perfume composition, and it comprises:
I) as defined above at least a The compounds of this invention as perfuming component;
The ii) at least a composition that is selected from fragrance carrier and perfumery base; And
The iii) at least a spices auxiliary agent of non-imposed selection.
Here, the meaning of " fragrance carrier " is to see the material that is actually a kind of neutrality from the viewpoint of perfumery, i.e. the organoleptic properties of its not obvious change perfuming component.Described carrier can be liquid or solid.
The limiting examples that can enumerate as liquid vehicle is emulsification system (being solvent and surfactant system), perhaps perfumery solvent commonly used.The feature of perfumery common solvent and the detailed description of type can not be exhaustive.But, can enumerate the most frequently used solvent such as dipropylene glycol, diethyl phthalate, Isopropyl myristate, peruscabin, 2-(2-ethoxy oxyethyl group)-1-ethanol or ETHYL CTTRATE as limiting examples.
As solid carrier, the limiting examples that can enumerate is absorption natural gum or polymkeric substance, or or even encapsulating material.The example of this class material can comprise wall-forming and plastification material, as monose, disaccharides or trisaccharide, native starch or treated starch, hydro-colloid, derivatived cellulose, polyvinyl acetate (PVA), polyvinyl alcohol, protein or pectin or in addition at reference such as H.Scherz, Hydrokolloids:Stabilisatoren, Dickungs-undGehermittel in Lebensmittel, Band 2der Schriftenreihe Lebensmittelchemie
Behr ' s VerlagGmbH ﹠amp; Co., Hamburg, the material of enumerating in 1996.Sealing is to well known to a person skilled in the art method, and can for example use as spraying drying, cohesion or the technology implementation of extruding in addition; Perhaps constitute by the bag that comprises cohesion and complex coacervation technology is encapsulated.
Here, the meaning of " perfumery base " is to comprise the composition that at least a perfuming furtherance divides.
It is not the compound of general formula (I) that described perfuming furtherance divides.In addition, here the meaning of " perfuming furtherance branch " is to be used in the compound of giving the pleasant sensation effect in perfuming preparation or the composition.In other words the furtherance branch is considered to a kind of perfuming component here, must be known as by those skilled in the art and can give or change the smell of composition in the mode of positive or pleasant, and be not only to have smell.
Characteristic and type that the perfuming furtherance that exists in the base-material divides here do not guarantee to describe in detail more, in no case may be exhaustive, and the technician can select it based on its general knowledge and according to the purposes of expection or the sensory effects of application and expectation.Generally speaking, these perfuming furtherances belong to different chemical classifications, be alcohol, aldehyde, ketone, ester, ether, acetic ester, nitrile, terpene hydrocarbon, nitrogenous or sulfur heterocyclic compound and essential oil, and described perfuming furtherance branch can be natural or synthetic sources.In any case many these perfuming furtherances are respectively in the reference works Perfume and FlavorChemicals as S.Arctander, 1969, Montclair, New Jersey, USA or its upgrade version, or other works of similar characteristics, and the patent documentation that enriches in the field of perfumery.Will be understood that also described furtherance branch can also be the known compound that discharges all kinds fragrance compound with controllable manner.
For the composition that comprises fragrance carrier and perfumery base simultaneously, except those previous detailed descriptions, suitable fragrance carrier can also be that ethanol, water/alcohol mixture, limonene or other terpenes, isoparaffin such as known trade mark are
(source: Exxon Chemical) those or glycol ethers and glycol ether-ether such as known trade mark are
(source: Dow Chemical Company) those.
Here, the meaning of " spices auxiliary agent " is to give the composition of extra additional benefits such as color, special photostabilization, chemical stability etc.Auxiliary agent characteristic commonly used and the detailed description of type in can not exhaustive perfuming base-material, but it should be noted that described composition is well known to a person skilled in the art.
According to specific embodiments of the present invention, (4Z)-4-laurylene nitrile that described composition can comprise and the weight ratio scope of dodecyl nitrile are about 80/20～95/5.
Except the perfume composition of at least a spices auxiliary agent that comprises at least a general formula (I) compound, at least a fragrance carrier, at least a perfumery base and non-imposed selection, the present composition of being made up of at least a general formula (I) compound and at least a fragrance carrier has represented specific embodiment of the present invention.
It should be noted that at this, it is important having the possibility that surpasses a kind of general formula (I) compound in the above-mentioned composition of mentioning, because it can make the spices dealer make blending stock, the spices of the smell aromatic with all cpds of the present invention, thereby be the new instrument of its work creation.
Preferably, any directly from the mixture (for example without abundant purification, wherein can contain The compounds of this invention as raw material, intermediate or product) of chemosynthesis, all can not be considered to according to perfume composition of the present invention.
In addition, The compounds of this invention also can be advantageously utilised in all areas of modern perfume industry, to give or to change the smell of the consumer's goods that wherein add described compound (I) energetically.Thereby the perfumed article that comprises following composition also is one object of the present invention:
I) compound of at least a aforesaid general formula (I) or perfume composition of the present invention are as perfuming component; And
Ii) consumer product base.
For the sake of clarity, it should be noted that here " consumer product base " meaning is a kind of consumer's goods compatible with perfuming component.In other words, perfumed article according to the present invention comprises the function prescription, and the additional useful auxiliary agent corresponding to the consumer's goods (for example sanitising agent or air freshener) of non-imposed selection, and at least a The compounds of this invention of sense of smell significant quantity.
Here do not guarantee to be described in more detail characteristic and the type of consumer's goods component, in any case it all can not be exhaustive, the technician can select it according to character and the desired result of described product based on its general knowledge.
The example of suitable consumer product base comprises all other goods commonly used in solid or liquid cleaner and fabric softening agent and the perfume industry, be perfume, Gu Longshui or aftershave lotion, perfumed soap, shower is used or bath in a tub salt, mousse, oil or gel, health product or hair care product such as shampoo, body care product, reodorant or antiperspirant, air freshener and also have cosmetic formulations.As sanitising agent, no matter they still design for industrial application for family, predetermined application is for example handled cleanser compositions or the cleaning product that designs for fabric, plate or stiff dough as for cleaning tableware or cleaning various surfaces.Other perfumed article be fabric refreshers, flatiron water, paper, cleaning piece or SYNTHETIC OPTICAL WHITNER.
Some above-mentioned consumer product base may be that compound of the present invention is had rodent medium, are not necessary by premature decomposition by sealing protection compound of the present invention for example therefore.
The ratio that can be sneaked into various said products or composition according to compound of the present invention changes a wide numerical range.These values depend on by the sensory effects of the character of the goods of perfuming and expection, and when compound according to the present invention and perfuming furtherance branch, solvent or this area additive commonly used mixes, the character of furtherance branch in given base-material.
For example, in the situation of perfume composition, based on the weight of the composition of having sneaked into The compounds of this invention, the typical concentration of The compounds of this invention is about 0.001%～1.0% weight, or even higher.When these compounds are sneaked into perfumed article, can use the concentration that is lower than this, as 0.01%～0.5% weight, percentage ratio is the weight with respect to goods.
The compounds of this invention can prepare like this, by well known to a person skilled in the art any method 4-dodecylene aldehyde is converted to corresponding oxime, and is non-imposed selectively by well known to a person skilled in the art that any method is converted to this oxime the nitrile of expection then.
Embodiment
Embodiment
The present invention will further describe by the mode of following embodiment now, and abbreviation wherein has the common implication in this area, temperature with degree centigrade (℃) expression; With 360 or the 400MHz instrument at CDCl
3Middle record (as not pointing out in addition)
1H and
13The NMR spectroscopic data of C, chemical shift δ are represented with ppm, are benchmark with TMS, and coupling constant J represents with Hz.
Embodiment 1
Synthesizing of compound (4Z)-4-laurylene aldoxime
Contain with 30 fens clockwise in the 250ml three-necked flask of 20g (the Z)-4-dodecylene aldehyde that is dissolved in the 50ml hexahydroaniline and add 8.4ml NH
2OH (50% the aqueous solution).Reaction continues a whole night.The organic layer decantation is gone out, and wash with water, vacuum is removed this solvent, obtains 1-E and 1-Z and be 55/45 mixture oxime.
MS (main isomer): m/z (%): 197[M+] (1), 180 (38), 178 (6), 152 (9), 138 (8), 136 (7), 124 (8), 122 (10), 112 (25), 96 (70), 95 (68), 82 (100), 67 (49), 55 (68), 43 (80), 41 (97).
MS (less important isomer): m/z (%): 180 (6), 152 (9), 138 (6), 136 (7), 124 (10), 122 (12), 110 (15), 108 (21), 96 (80), 95 (74), 82 (96), 67 (53), 55 (70), 43 (88), 41 (100).
(4Z)-that 4-laurylene nitrilation can thing is synthetic
The above oxime that obtains is charged in the flask that contains 20ml Glacial acetic acid and 0.2g Potassium ethanoate.100 ℃ of reacting by heating 1 hour, cooling at room temperature then, hydrolysis is also used Et
2The O extraction.Organic layer washes three times with water, and uses MgSO
4Drying, concentrated solvent.Flash chromatography purifying (hexahydroaniline/vinyl acetic monomer=97/3) obtains the pure nitrile of 14.2g (productive rate 72%).
1H-NMR：0.88(t，J＝7，3H)，1.24-1.40(m，10H)，2.05(q，J＝7，2H)，2.35-2.43(m，4H)，5.37(m，1H)，5.56(m，1H).
13C-NMR：14.1(q)，17.6(t)，22.7(t)，23.3(t)，27.3(t)，29.2(t)，29.3(t)，29.5(t)，31.9(t)，119.4(s)，125.0(d)，133.7(d).
Embodiment 2
The preparation of perfume composition
Prepare orange odor type perfume composition by mixing following composition:
The composition weight part
Jasmal 60
C10 aldehyde 15
C12 aldehyde 30
C8 aldehyde 5
C9 aldehyde 5
MNA aldehyde 10
9-undecenal 10
Citral 10
3,7-dimethyl-6-octene nitrile 20
Allyl oenanthate 5
Linalool 200
Methyl methylanthranilate 30
200
Firpene 20
Superfine orange terpenes 200
Terpinol
80
1000
1) methyl dihydrojasmonate; Source: Firmenich SA, Geneva, Switzerland
2) (S)-2-(1,1-dimethyl propoxy-) propyl propionate; Source: Firmenich SA, Geneva, Switzerland
Add 10% solution of (4Z)-4-laurylene nitrile in dipropylene glycol of 10 weight parts to above-mentioned perfume composition, give the fabulous natural orange feature that the latter makes us remembering best Sicily orange smell consumingly.
When adding (4Z)-4-dodecylene aldehyde of same amount in above-mentioned composition, new fragrance is nature more not, and fragrance is acid and more not mature, and namely its orange feature is compared very different with the feature that contains nitrile of the present invention.
When adding the dodecyl nitrile of same amount in above-mentioned perfuming base-material, the smell of said composition has lost the orange feature, becomes more not graceful, has more functionalized and fatty feature.
Embodiment 3
The preparation of perfume composition
By mixing the lady's perfume composition that following composition prepares the east odor type:
The composition weight part
Jasmal 20
50%
*Styryl carbinol 10
Hexyl cinnamic aldehyde 10
50%
*St-yrax (Benjoin) essential oil 30
Citrus bergamia essential oil 50
8-methoxyl group-2,6,6,8-tetramethyl--three ring [5.3.1.0 (1,5)] undecane 10
Lemon quintessence oil 15
10%
*Civet (Civette) 15
4-cyclohexyl-2-methyl-2-butanols 20
Tonka bean camphor 15
10%
*Naphthane (Decal) 10
10%
*Vanillal 20
Oxymethoxyallylbenzene 10
Laurine 35
10%
*Jasmin quintessence oil 25
Linalool 40
Orange essential oil 25
Moschus ketenes (Muscenone)
3)50
10%
*(E)-4-(2,2, C-3, T-6-tetramethyl--R-1-cyclohexyl)
-3-butene-2-ketone 10
Herba Pogostemonis essential oil 40
10%
*Peru balm (Perou baume) 30
Benzyl salicylate 260
(Z)-3-hexene-1-base salicylate 25
Vanillin 10
Vetiveria zizanoides 10
10%
*Yilan essence
25
990
*In the dipropylene glycol
1) methyl dihydrojasmonate; Source: Firmenich SA, Geneva, Switzerland
2) 1-(octahydro-2,3,8,8-tetramethyl--2-naphthyl)-1-ethyl ketone; Source: InternationalFlavors ﹠amp; Fragrances, the U.S.
3) 3-methyl-(4/5)-cyclopentadecylene ketone; Source: Firmenich SA, Geneva, Switzerland
4) 3,3-dimethyl-5-(2,2,3-trimethylammonium-3-cyclopentenes-1-yl)-4-amylene-2-alcohol; Source: Firmenich SA, Geneva, Switzerland
5) (S)-2-(1,1-dimethyl propoxy-) propyl propionate; Source: Firmenich SA, Geneva, Switzerland
6) banana aldehyde base-material (floral type); Source: Firmenich SA, Geneva, Switzerland
1% solution of (4Z)-4-laurylene nitrile in dipropylene glycol that adds 10 weight parts is to above-mentioned perfume composition, and certain degree has strengthened the Citrus-orange feature of natural succulence of the gentleness of this east spices.
When (the 4Z)-4-dodecylene aldehyde that adds same amount to above-mentioned composition or dodecyl nitrile, viewed difference and above-mentioned similar.
Claims (11)
1. the compound of a general formula (I),
Wherein, X represents the CN group, carbon-carbon double bond be configured as E or Z or their mixed form.
2. the compound according to claim 1 is characterized in that it is isomer (4Z) and mixed form (4E), and their ratio ranges is 80/20 ~ 99.5/0.5.
3. (4Z)-4-laurylene nitrile is as the compound of claim 1.
4. (4Z)-4-laurylene aldoxime.
5. a perfume composition comprises
I) at least a compound as each definition of claim 1 ~ 4;
The ii) at least a composition that is selected from fragrance carrier and perfumery base; And
The iii) at least a spices auxiliary agent of non-imposed selection.
6. perfume composition according to claim 5 is characterized in that comprising the weight ratio scope and is 80/20 ~ 95/5 (4Z)-4-laurylene nitrile and dodecyl nitrile.
7. perfumed article comprises:
I) at least a as perfuming component as in the compound of general formula (I) compound of each definition of claim 1 ~ 3 and claim 4 definition; And
Ii) consumer product base.
8. the perfumed article according to claim 7 is characterized in that consumer product base is solid or liquid cleaner, fabric softening agent, perfume, hair care product, body care product, air freshener, cosmetic formulations, fabric refreshers, flatiron water, paper, cleaning piece or SYNTHETIC OPTICAL WHITNER.
9. the perfumed article according to claim 7 is characterized in that consumer product base is health product.
10. the perfumed article according to claim 7 is characterized in that consumer product base is Gu Longshui, aftershave lotion, and perfumed soap, shower is used or bath in a tub salt, mousse, oil or gel, shampoo, reodorant or antiperspirant.
11. as the compound of general formula (I) compound of each definition of claim 1 ~ 3 or the claim 4 definition purposes as perfuming component.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB2007051354 | 2007-04-16 | ||
| WOPCT/IB2007/051354 | 2007-04-16 | ||
| IBPCT/IB2007/051354 | 2007-04-16 | ||
| PCT/IB2008/051109 WO2008125994A1 (en) | 2007-04-16 | 2008-03-25 | 4-dodecene derivatives as perfuming ingredients |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101657413A CN101657413A (en) | 2010-02-24 |
| CN101657413B true CN101657413B (en) | 2013-08-14 |
Family
ID=39671383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200880012003XA Active CN101657413B (en) | 2007-04-16 | 2008-03-25 | 4-dodecene derivatives as perfuming ingredients |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7985403B2 (en) |
| EP (1) | EP2137138B1 (en) |
| JP (1) | JP5399376B2 (en) |
| CN (1) | CN101657413B (en) |
| BR (1) | BRPI0808777A2 (en) |
| ES (1) | ES2397666T3 (en) |
| MX (1) | MX2009010812A (en) |
| WO (1) | WO2008125994A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5912943B2 (en) * | 2012-07-10 | 2016-04-27 | 花王株式会社 | 3,7-dimethyl-2-methylene-6-octenenitrile |
| US10449433B1 (en) * | 2018-04-29 | 2019-10-22 | Walter Judson Bennett | Wave energy and rip current control system for surf pools |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0672746A1 (en) * | 1994-03-18 | 1995-09-20 | Givaudan-Roure (International) S.A. | Oxime ethers and perfume and flavouring compositions containing them |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960923A (en) | 1973-12-03 | 1976-06-01 | Rhodia, Inc. | Process for the preparation of α,β-unsaturated nitriles |
| NL7713925A (en) | 1977-12-15 | 1979-06-19 | Naarden International Nv | 4-Deceno:nitrile used as fragrance - in perfumes and perfumed products |
| JPS57134457A (en) | 1981-02-16 | 1982-08-19 | Dainippon Ink & Chem Inc | Polyprenyl acetoxime derivative and its preparation |
| JPS5855410A (en) * | 1981-09-03 | 1983-04-01 | ユニリ−バ−・ナ−ムロ−ゼ・ベンノ−トシヤ−プ | Perfume composition containing fatty nitrile |
| DE3932325A1 (en) * | 1989-09-28 | 1991-04-11 | Haarmann & Reimer Gmbh | ALKADIENNITRILE, PROCESS FOR THEIR PREPARATION AND THEIR USE |
| EP1174116A1 (en) * | 2000-07-21 | 2002-01-23 | Givaudan SA | Fragrance composition comprising a mixture of nitriles |
| JP2004528289A (en) | 2001-01-26 | 2004-09-16 | クエスト・インターナショナル・ビー・ブイ | Aromatic compounds |
| DE10110858A1 (en) * | 2001-03-07 | 2002-09-12 | Cognis Deutschland Gmbh | 2,3,5,5-tetramethylhexanal derivatives |
| EP1687261A4 (en) | 2003-11-12 | 2007-09-05 | Flexitral Inc | Novel oxy-nitriles |
| JP5248114B2 (en) | 2004-12-08 | 2013-07-31 | ジボダン エス エー | Organic compounds |
-
2008
- 2008-03-25 US US12/530,779 patent/US7985403B2/en active Active
- 2008-03-25 EP EP08719825A patent/EP2137138B1/en active Active
- 2008-03-25 JP JP2010503629A patent/JP5399376B2/en not_active Expired - Fee Related
- 2008-03-25 WO PCT/IB2008/051109 patent/WO2008125994A1/en active Application Filing
- 2008-03-25 ES ES08719825T patent/ES2397666T3/en active Active
- 2008-03-25 BR BRPI0808777-6A patent/BRPI0808777A2/en not_active IP Right Cessation
- 2008-03-25 CN CN200880012003XA patent/CN101657413B/en active Active
- 2008-03-25 MX MX2009010812A patent/MX2009010812A/en active IP Right Grant
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0672746A1 (en) * | 1994-03-18 | 1995-09-20 | Givaudan-Roure (International) S.A. | Oxime ethers and perfume and flavouring compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2137138A1 (en) | 2009-12-30 |
| ES2397666T3 (en) | 2013-03-08 |
| WO2008125994A1 (en) | 2008-10-23 |
| BRPI0808777A2 (en) | 2014-08-19 |
| JP2010524916A (en) | 2010-07-22 |
| JP5399376B2 (en) | 2014-01-29 |
| US7985403B2 (en) | 2011-07-26 |
| CN101657413A (en) | 2010-02-24 |
| EP2137138B1 (en) | 2012-10-31 |
| US20100008881A1 (en) | 2010-01-14 |
| MX2009010812A (en) | 2009-10-29 |
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